Why does the discrepancy measure involve a supremum over the hypothesis space?
The formula $G=\mathbb{E}\left[ f(Z_{T+1}) \mid \mathbf{Z}_1^T\right] - \sum_{t=1}^Tq_t \mathbb{E}\left[ f(Z_t) \mid \mathbf{Z}_1^{t-1} \right]$ actually represents a set, for all possible values of $f$. Therefore, $\text{disc}(\mathbf{q}) = \operatorname{sup}_{f \in \mathcal{F}} \left( \mathbb{E}\left[ f(Z_{T+1}) \mid \mathbf{Z}_1^T\right] - \sum_{t=1}^Tq_t \mathbb{E}\left[ f(Z_t) \mid \mathbf{Z}_1^{t-1} \right] \right)$ is the element not necessarily in that set $G$ that is greater than all elements in that set $G$, but is the smaller than any other element that is greater than any element in that set $G$. In other words, $\text{disc}(\mathbf{q})$ represents an upper bound on the discrepancy $G$, but it is the smallest possible upper bound. See also this answer for more details about the supremum and the relationship between the supremum and upper bounds.

So, unless I am wrong, this is not necessarily a worst-case analysis (but I am not even sure how one would define the worst-case analysis in this context), but we are looking for the smallest upper bound. In the context of algorithms, the worst-case analysis is with respect to the input (i.e. the worst-case input), but you can have upper or lower bounds for worst and best-case scenarios. See, for example, this answer that illustrates this. Why do we want an upper bound? Because we can be certain that we won't have a generalization error worse than it. You can't do this with e.g. a lower bound.